This thesis serves to bring Iceland into the realm of Nordic family-demographic and fertility research. Based on event-history techniques applied to Iceland longitudinal register data, I provide an overview of contemporary family-demographic trends during the last few decades. The thesis consists of four empirical studies. In Study I, I examine the childbearing trends in Iceland during 1982–2013. I find evidence of postponed motherhood during this period, with increases in fertility rates for women in their 30s and 40s. The propensity to have a second and third child did not decline during the study period; on the contrary, these birth intensities have increased since the mid-1980s. During a period of increased educational attainment and postponed family formation, the resilience of Icelandic fertility is intriguing. Study II provides further insight into recent childbearing dynamics in Iceland and how they may be linked to social-policy reforms and the intervention of the economic crisis in 2008. The findings indicate that changes in standardized birth rates coincided with a reformed family-policy package: A declining trend in standardized first-birth rates came to a halt, and the propensity to have a second and a third child increased. After the onset of the economic crisis, a trend of decreasing first-birth intensities reemerged, which was followed by declining second- and third-birth rates as well. The development in the post-2008 period indicates that even in the most gender-equal settings, the gender balance in family care is still fragile. Study III addresses the high nonmarital birth rate in Iceland. Nowhere in Europe is premarital childbearing as pervasive. Roughly 70% of children were born to unwed mothers in 2018, which, on the surface, puts Iceland at the vanguard of a development often associated with a Second Demographic Transition. In this study I investigate the union-formation behavior during a period of 20 years with the objective to gain insight into the interplay of childbearing, cohabitation, and marriage. I find a forceful postponement of registered cohabitation over time, but a stable portion of around 80% of women registering cohabitation. Around 70% of women have married by age 45, and the standardized marriage rates remained relatively stable during the study period. The findings suggest that within a context such as the Icelandic one most people eventually tend to marry, regardless of the prevalence of cohabitation. I suggest that registered cohabitation should be seen as providing a semi-regulated union status for prospective parents in relation to their childbearing. Marriage, on the other hand, could be seen as providing an elevated union status to couples. In Study IV the focus is on marital dissolution. Research findings usually suggest that premarital cohabitation is associated with increased risk of marital break-up. Data on registered cohabitation enable us to investigate the proposed association from a new perspective. The data allow us to focus on couples that intend to live together while weeding out couples that merely “drift” into coresidential unions. The estimates indicate that premarital registered cohabitation in Iceland is associated with lower risk of marital break-up, and that this finding is very robust. I interpret the Icelandic-specific findings in support of a trial marriage hypothesis, suggesting that premarital cohabitation produces lower risks of divorce.